Startup Therapy

Hosted by Startups.com

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344

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Aug 2026

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About the show

The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.

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August 17, 2026Episode 34333 min

How to be a Horrible Startup Advisor

Ever gotten startup advice that sounded like a fact—but was really just someone’s confident opinion? This episode breaks down why so much startup advice is dangerous, especially from well-meaning advisors who lack self-awareness about their bias and the weight their words carry. Ryan and Will unpack how founders, who often can’t tell “ground truth” from bravado, can be pushed into bad decisions by overconfident feedback—particularly from investors and local “yokels” with narrow worldviews. They share examples from pitch competitions and boardrooms, argue that delivery is often more harmful than the advice itself, and highlight “you might consider” as a simple way to add humility and optionality. The key takeaway: great advisors avoid ego, disclose uncertainty, and help founders synthesize perspectives rather than obey directives. 00:00 Why Advice Needs A Test 01:17 Confidence Becomes Fact 03:39 Pitch Judge Hyperbole 10:30 VC Power Dynamics 15:10 Advice Not Facts 17:03 You Might Consider 18:28 Conflicting Perspectives 22:53 Bias And Obedience 28:07 Do No Harm 32:59 Community Outro Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

August 3, 2026Episode 34243 min

Which Version of Me is Coming to Dinner Tonight

Ever wonder which “version of you” should show up to dinner, a board meeting, or a team update? This episode breaks down why founders feel like they’re constantly auditioning different personas—optimistic forecaster, calm leader, guarded partner—because the honest answer (“I don’t know” or “we’re struggling”) can carry real consequences with investors, employees, customers, friends, and family. The conversation explores the difference between confidence about an uncertain future versus crossing into deception, the emotional burn rate founders pay to stay composed, and how compartmentalization becomes muscle memory—even through illness, grief, or shutdowns. They highlight how group dynamics push founders to match the room’s tone, and why having one place to take the mask off—like a trusted founder group—can be essential to staying sane and healthy. 03:27 First Pitch Meeting Lesson 04:33 Choosing What To Share 07:26 Buckets Of Consequence 15:54 Gray Area Of Belief 19:07 Founder Pressure Cooker 20:50 Founder Groups And Leaks 27:55 Working Through Pain 30:52 Joy Versus Consequence 36:23 Honesty Sets The Tone 42:06 You’re Not Alone Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

July 20, 2026Episode 34143 min

The Death of the Technical Cofounder

What if you could build a working prototype without giving away half your company? The episode argues that tools like Claude have ended the old “technical co-founder as early-stage gatekeeper” dynamic: founders used to need a developer to cross the first binary hurdle from idea to product, and some investors also pushed for technical co-founders before funding. Now, founders can ship prototypes in a weekend with an AI subscription, pushing the vulnerability window later and repricing equity. The hosts stress technical talent still matters—especially for scaling and real engineering—but AI exposes the difference between people who only had scarce, auditable-by-no-one skills and those with true product, systems, and architecture value. They compare this shift to past disruptions like TemplateMonster commoditizing million-dollar websites, predicting a sorting of technical roles and a “new” bionic technical co-founder focused more on architecture than gatekeeping. What to listen for: 00:47 Claude Ends the Requests 03:14 The Old Quest for Coders 07:50 When Coding Got Too Hard 10:16 VC Bias Toward Technical 21:59 Prototype Value Myth 29:32 Chaff Skills Explained 31:04 Builders Get The Rocket 42:27 Golden Era For Founders 42:50 Bionic Co Founder Future Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

July 14, 2026Episode 34035 min

We Do What Other's Won't

What are you actually willing to do to get what you want as a founder? Using Will’s 6:00 a.m., 15-degree framing session and a dumpster-diving Bobcat mishap as metaphors, this episode breaks down what separates founders from everyone else: an “unreasonable” willingness to do hard, risky, uncomfortable things repeatedly—often without any guarantee of payoff. The conversation explores the real price founders pay (uncertainty, rejection, sacrifice, and daily grind), why high achievers used to clear reward loops can struggle in startup chaos, and why outsized outcomes tend to follow people who endure what others won’t. They also unpack common misconceptions about wealth and merit through examples like Jason Calacanis, Elon Musk, and elite athletes, and argue that the deeper reward isn’t money—it’s autonomy and ownership of your outcome. What to listen for: 02:13 Nothing I'm Not Willing to Do 04:41 Why Founders Get Paid 09:47 Rejection and Being Wrong 12:31 High Achievers vs Founders 15:58 Building the Willingness Muscle 18:45 Willingness Beats Talent 29:36 Real Reward Is Autonomy 32:51 Aspiring Founder Reality Check 34:52 Worth It in the End Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

July 6, 2026Episode 33938 min

Everyone is a startup... Again

What happens when AI turns your hard-won moat into a weekend project? This episode argues that AI has effectively forced established companies back into “startup mode,” wiping out long-held assumptions about products, staffing, and competitive advantage. Will and Ryan break the reset into three shifts: the cost to build and operate has collapsed, big teams and legacy systems have become liabilities, and “everything is buildable” faster than incumbents can adapt. They warn that competitors can now reach product parity quickly and survive with tiny teams that don’t have payroll to protect, making old “wait them out” strategies obsolete. The hardest part is the human reset: org charts, roles, and business models must change even when it means cannibalizing what currently pays the bills. The companies that survive are those willing to restart deliberately, think like founders again, and use experience as the edge. 01:09 Moats Filled Overnight 02:57 Three Switches Flipped 04:07 Startups.com Case Study 06:48 Speedrun Not Disruption 10:01 Competitors That Never Die 16:45 The Staffing Reckoning 17:28 Answers Already Exist 18:00 AI Pivot People Fallout 20:05 Hard Reset Reality 23:10 Big Company Politics 34:09 Level One With XP 36:03 Founders Win Again Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

June 30, 2026Episode 33848 min

Where were you when I was broke?

Ever notice how people show up loudest after you’ve already won? This episode digs into why founders often get the least support when the risk is highest—and the most opinions once success is “de-risked.” Will shares early moments of having virtually no safety net (including starting with $19, dropping out, and getting doubted), contrasted with the few timely “bricks” that actually changed his trajectory—like a risky $10K loan and a friend’s family offering a place to stay for the holidays. They unpack how funding wins, press, and exits attract late-arriving fans, opportunists, and advice that can derail post-success decisions, and why founders should take inventory of who truly showed up when things looked impossible—and be that kind of support for other founders. 00:39 Elon Money Opinions 02:55 Guidance Counselor Doubt 04:13 Early Support Matters 05:44 Nineteen Dollars Start 06:53 Ten Thousand Loan 09:55 Wide Angle Victory 10:38 Doubt Chokes Founders 11:38 Young Founder Respect 14:59 I Told You So Bias 18:49 Funding Round Whiplash 20:20 Recruiters Disappear 21:30 Success Rewrites History 23:03 Sam Altman Backlash 25:40 Founders After Success 28:32 Timing Is Support 32:00 Must Be Nice Myth 35:56 Bricks in Foundation Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

June 23, 2026Episode 33754 min

What if I'm the Best, but don't know it?

What if building a company is the fastest way to find out what you’re actually capable of? This episode explores how startups don’t just get built by founders—startups build founders by forcing them into new roles like finance, sales, marketing, design, legal, and leadership, often before they feel ready. Will shares how real stakes (like cash flow and payroll) turned “I’m bad at math” into practical financial skill, and why getting to ~80% proficiency across key areas creates leverage, better decision-making, and protection against getting bullshitted. The conversation digs into how exposure and environment unlock hidden potential (from Lars Ulrich’s story to personal career turning points), why most “I can’t” is really “I haven’t,” and how repeated reps, feedback, and humility turn competence into confidence—plus a cautionary backup-dancer story about confidence without practice. What to listen for: 02:10 Creating Your Own Role 03:59 From Math Failure to Finance 07:04 Asking Dumb Money Questions 09:35 Become What Company Needs 10:47 The 80 Percent Rule 11:42 Agency Skills Stack 15:12 Cross Skill Superpowers 16:44 No One Can Bullshit You 19:05 AI as Private Tutor 20:13 Exposure Creates Greatness 27:03 Defining Moments Reframed 29:18 Dad Versus Computers 32:48 Reinventing Your Identity 39:26 Founder Reinvention Loop 42:27 Craftsmanship And Parenting 45:36 Dance Off Reality Check 52:28 What If And Keep Moving Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

June 15, 2026Episode 33633 min

Founders Don't Retire

What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: founders are wired to create, not to consume, and the fantasy of beach life usually shows up at a low-energy point when what’s really needed is recovery. They compare founder burnout to wanting the finish line without running the race, and note how exits often lead from “margaritas” to “domain names” within months because the calling returns once the nervous system resets. The key reframe: separate a recovery plan from a retirement plan, and define “retirement” as creating on your own terms—less panic, fewer hated parts (like investor pressure or endless hours), more control, and a sustainable way to keep doing the work you love. What to listen for: 00:49 Builder DNA and Relief 00:57 Carpenter Story and Pain 03:06 Four Minute Founder Brain 04:31 Broken Retirement Dream 05:13 Reload and Retire Again 06:31 Beach Metaphor Explained 09:58 Athletes vs Founder Longevity 12:00 Vacation Checklist Trap 15:35 No Substitute for Mission 17:29 Finish Line Fantasy 18:45 Recovery Not Retirement 20:35 Builders Need Purpose 25:14 Retired But Uncharged 27:00 Creation Over Consumption 30:16 Retirement On Your Terms 32:26 Design Better Circuits Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

June 8, 2026Episode 33538 min

The Right Time to Start is Right Now

Ever feel like you’re “almost ready” to launch—just one more feature, plan, or credential away? This episode argues that “ready” isn’t a prerequisite for startups; it’s the result of starting and getting real market feedback. Using examples like selling early software for $1,500, learning web building on the fly, a disastrous (but educational) client pitch moment, and even an impulsive scuba dive, the discussion shows why planning can become productive-looking theater when nothing is being tested. The real cost of waiting isn’t just lost time—it’s lost learning, missed customers, and negative compounding versus competitors who take action. Planning has value only when it directly leads to action, because failure and iteration are the mechanism that reveals what works. What to listen for: 01:14 Plans Meet Reality 02:00 Readiness Comes After 02:34 First Founder Breakthrough 07:41 Micro Center Origin Story 10:07 Cost of Waiting 11:14 Planning Versus Theater 12:23 Test With Customers 14:09 Ecommerce Pitch Fail 16:41 Whiteboard Versus Field 18:48 Learning By Building 19:35 Learn By Doing 20:05 Founder Skill Stack 20:45 Econ 101 Mindset Shift 22:45 Human Potential Unlocks 24:27 Momentum Beats Certainty 25:58 Plan To Learn Fast 30:26 Conditioned To Avoid Failure 34:34 Cost Of Waiting 35:50 Action Over Perfection 36:47 Stop Waiting Start Now Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/

June 1, 2026Episode 33446 min

The Most Expensive Equity Doesn't go to Investors

Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade because cash and terms are clear, while “everyone else pays in maybes and promises.” It warns that early-stage equity feels worthless but represents 100% of a company’s future value, so giving away 50% to a near-stranger can become a permanent cap table problem that also costs speed, optionality, and sanity. Practical fixes include vesting, cliffs, tying equity to real value creation, defining what happens if someone stops contributing, and putting breakup terms in writing early. The discussion also critiques employee equity as time-based rather than performance-based, and advisor equity as often unaccountable, where tiny percentages can hide very expensive outcomes. What to listen for: 00:00 Investor vs Founder Equity 01:26 Equity Is Priceless 03:43 Co-Founder Split Hangover 06:04 Why People Underperform 11:15 Fairness Turns To Resentment 12:44 Will's Unsubscribe Story 15:53 Vesting And Breakup Terms 18:17 Early Employees Option Pool 20:26 Equity As Compensation Trade 21:59 Paying Twice With Equity 22:14 Does Equity Change Effort 23:10 Lottery Ticket Reality 27:23 Equity Rewards Three Things 27:37 Advisor Equity Math 31:00 Reputation Versus Contribution 33:30 Network Intros Social Capital 35:56 Advice Has Shelf Life 40:24 Pricing Advisor Time 44:06 Treat Shares Like Cash Resources: Startup Therapy Podcast https://www.startups.com/community/startup-therapy Website https://www.startups.com/begin LinkedIn https://www.linkedin.com/company/startups-co/ Join our Network of Top Founders Wil Schroter https://www.linkedin.com/in/wilschroter/ Ryan Rutan https://www.linkedin.com/in/ryan-rutan/